A crowded beach with people sunbathing and swimming.

Southwest Florida Adventure Vacations

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Adventure vacation packages in Southwest Florida

Price found within the past 48 hours. Click for updated prices.
  • Sept 16 - Sept 20

    The Perry Hotel Naples + Flight

    Naples
    4 nights
    4.5 star property
    9.6/10 - Exceptional (999 reviews)
    "We would definitely book this hotel again!"
    Reviewed August 6, 2026
    Roundtrip Toronto (YTO) - Fort Myers (RSW)
    YYZ - FLL1 stop FLL - YYZ1 stop
    CA $881
    CA $609
    per traveller
    found 1 day ago
    The Perry Hotel Naples
  • Oct 8 - Oct 13

    Cedar Cove Resort and Cottages + Flight

    Holmes Beach
    5 nights
    3.0 star property
    9.2/10 - Wonderful (569 reviews)
    "Stayed for one night everything was in place very well thought off and cosy and very clean love the swing just out the door and seeing the shells all over and beach was amazing shower and beach chairs was in place staff was very friendly and had a home feeling I will be back"
    Reviewed August 5, 2026
    Roundtrip Montreal (YUL) - Tampa (TPA)
    YUL - TPA1 stop TPA - YULNonstop
    CA $3,935
    CA $2,753
    per traveller
    found 1 day ago
    Cedar Cove Resort and Cottages
  • Sept 9 - Sept 14

    Marriott Sanibel Harbour Resort & Spa + Flight

    Punta Rassa
    5 nights
    4.0 star property
    8.6/10 - Excellent (1,013 reviews)
    "Very clean, the room is very spacious and comfortable and the staff is super friendly, I recommend 100%"
    Reviewed August 5, 2026
    Roundtrip Hamilton (YHM) - Fort Myers (RSW)
    YHM - MCO1 stop MCO - YHM1 stop
    CA $1,375
    CA $1,060
    per traveller
    found 23 hours ago
    Marriott Sanibel Harbour Resort & Spa
  • Sept 13 - Sept 16

    Manasota Key Resort + Flight

    Manasota Key
    3 nights
    2.5 star property
    9.4/10 - Exceptional (307 reviews)
    "Our stay at Manasota Key Resort was absolutely excellent. We stayed in a one-bedroom Gulf-view unit in the main building, and the views were beautiful. The resort was incredibly quiet, clean, and spacious, with plenty of room to relax. The bed was very comfortable, although the sofa bed was not quite as comfortable. The unit had a huge refrigerator and a fully stocked kitchen with appliances, dishes, and utensils, which made the stay feel even more convenient. The staff was attentive, friendly,..."
    Reviewed August 3, 2026
    Roundtrip Montreal (YUL) - Fort Myers (RSW)
    YUL - SRQ1 stop SRQ - YUL1 stop
    CA $1,755
    CA $1,366
    per traveller
    found 1 day ago
    Manasota Key Resort
  • Sept 16 - Sept 20

    Lani Kai Beachfront Resort + Flight

    Fort Myers Beach
    4 nights
    3.5 star property
    8.8/10 - Excellent (1,865 reviews)
    "Room was in need of updating. Tiny pillows on a King bed is just wrong."
    Reviewed August 6, 2026
    Roundtrip Toronto (YTO) - Fort Myers (RSW)
    YYZ - FLL1 stop FLL - YYZ1 stop
    CA $953
    CA $744
    per traveller
    found 1 day ago
    Lani Kai Beachfront Resort

Discover the most popular places to visit in Southwest Florida

What to do in Southwest Florida

Top Adventure Southwest Florida Hotels

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently Asked Questions

How much does a Southwest Florida vacation package cost?

Less than you might think — from just CA $609, in fact! By bundling flights, hotels and car rentals into your own custom-built vacation package, your getaway to Southwest Florida is just a few clicks away.

How do I get a cheap travel package to Southwest Florida?

Browse and book everything in the one place with our Southwest Florida vacation packages. We have incredible bargains on flights, hotels and more that'll keep your pocket happy and your spirit of adventure alive. And, with more than 550 partner airlines and 1,000,000 properties worldwide to select from, you'll have the flexibility to mix and match all you want.

Where should I stay in Southwest Florida?

You can't go past Tampa, with terrific landmarks including Raymond James Stadium and University of South Florida to discover. Or, if sights like Edison and Ford Winter Estates and Sun Splash Water Park are more your scene, Fort Myers is the place for you.

What are the top hotels in Southwest Florida?

Naples Grande Beach Resort and La Quinta Inn & Suites by Wyndham Naples East (I-75) know how to make their guests feel welcome in Naples. If your itinerary also includes Cape Coral, take a look at Trianon Bonita Bay and Sanibel Island Beach Resort. Both are very popular with travelers.

How far in advance should I book my Southwest Florida vacation?

Get rewarded with the widest variety at the cheapest prices by booking your vacation to Southwest Florida nice and early. Air carriers generally advertise tickets around a year before departure, so reserve your spot as soon as possible. That being said, Expedia is dedicated to providing you with the best deals around, so there's never a bad time to book your dream vacation!

What does an Expedia Southwest Florida travel package include?

That mostly depends on you. You can select from a range of Southwest Florida bundles, such as a flight, hotel and rental car. You can also book a hotel and a flight, or a flight and a rental car. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your perfect Southwest Florida vacation looks like, you're sure to save!

What should I know before booking a Southwest Florida travel package?

You can save a tidy sum by combining your flights, hotels and rental cars. Once you've made your booking, add on fun stuff like activities or tours. Your next awesome vacation is only a couple of clicks away.

Can I choose my airline with a Southwest Florida Expedia vacation package?

Yes — that's the beauty of an Expedia package. You're the boss! We have access to more than 550 partner airlines all over the world, so you have options galore when putting together your Southwest Florida escape.

If I'm not able to travel, can I cancel my Southwest Florida vacation package?

It's hard to predict what the future holds, so it's good to know that you can cancel or change your Southwest Florida vacation package. If you made your booking in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.